Literature DB >> 30603820

First virtual screening and experimental validation of inhibitors targeting GES-5 carbapenemase.

Francesca Spyrakis1, Pierangelo Bellio2, Antonio Quotadamo3, Pasquale Linciano3, Paolo Benedetti4,5, Giulia D'Arrigo6, Massimo Baroni7, Laura Cendron8, Giuseppe Celenza2, Donatella Tondi9.   

Abstract

The worldwide spread of beta-lactamases with hydrolytic activity extended to last resort carbapenems is aggravating the antibiotic resistance problem and endangers the successful antimicrobial treatment of clinically relevant pathogens. As recently highlighted by the World Health Organization, new strategies to contain antimicrobial resistance are urgently needed. Class A carbapenemases include members of the KPC, GES and SFC families. These enzymes have the ability to hydrolyse penicillins, cephalosporins and carbapenems, while also being less susceptible to available beta-lactam inhibitors, such as clavulanic acid. The KPC family is the most prevalent. It is mostly found on plasmids in Klebsiella pneumoniae, meaning that great amounts of attention, in terms of inhibitor design and structural biology, have been dedicated to it, whereas no efforts have yet been dedicated to GES-type enzymes, despite their ability to rapidly and horizontally disseminate. We herein report the first in silico screening against GES-5, which is the most dangerous GES-type beta-lactamase, using a library of 800K commercially available candidates that all share drug-like properties, such as their MW, logP, rotatable bonds and HBA/HBD atoms. The best screening results were filtered to enrich the number of different chemotypes, and then submitted to molecular docking. The 34 most promising candidates were selected for in vitro validation in biochemical assays against recombinant GES-5. Six hits acted as inhibitors, in the high micromolar range, towards GES-5 and led to the identification of the first, novel chemotypes with inhibitory activity against this clinically relevant carbapenemase.

Entities:  

Keywords:  Antibiotic resistance; Carbapenemases; Docking; GES-5 Guyana extended-spectrum-lactamase; In vitro inhibition; Virtual screening

Mesh:

Substances:

Year:  2019        PMID: 30603820     DOI: 10.1007/s10822-018-0182-2

Source DB:  PubMed          Journal:  J Comput Aided Mol Des        ISSN: 0920-654X            Impact factor:   3.686


  41 in total

1.  X-ray analysis of the NMC-A beta-lactamase at 1.64-A resolution, a class A carbapenemase with broad substrate specificity.

Authors:  P Swarén; L Maveyraud; X Raquet; S Cabantous; C Duez; J D Pédelacq; S Mariotte-Boyer; L Mourey; R Labia; M H Nicolas-Chanoine; P Nordmann; J M Frère; J P Samama
Journal:  J Biol Chem       Date:  1998-10-09       Impact factor: 5.157

2.  Structural basis for progression toward the carbapenemase activity in the GES family of β-lactamases.

Authors:  Clyde A Smith; Hilary Frase; Marta Toth; Malika Kumarasiri; Kwame Wiafe; Jared Munoz; Shahriar Mobashery; Sergei B Vakulenko
Journal:  J Am Chem Soc       Date:  2012-11-16       Impact factor: 15.419

3.  Unusual diversity of acquired β-lactamases in multidrug-resistant Pseudomonas aeruginosa isolates in a Mexican hospital.

Authors:  Jane Castillo-Vera; Rosa María Ribas-Aparicio; Carlos Juan Nicolau; Antonio Oliver; Lourdes Osorio-Carranza; Gerardo Aparicio-Ozores
Journal:  Microb Drug Resist       Date:  2012-05-03       Impact factor: 3.431

4.  Phenylboronic Acid Derivatives as Validated Leads Active in Clinical Strains Overexpressing KPC-2: A Step against Bacterial Resistance.

Authors:  Giuseppe Celenza; Mattia Vicario; Pierangelo Bellio; Pasquale Linciano; Mariagrazia Perilli; Antonio Oliver; Jesús Blazquez; Laura Cendron; Donatella Tondi
Journal:  ChemMedChem       Date:  2018-02-20       Impact factor: 3.466

5.  Extending pKa prediction accuracy: high-throughput pKa measurements to understand pKa modulation of new chemical series.

Authors:  Francesca Milletti; Loriano Storchi; Laura Goracci; Stefanie Bendels; Bjoern Wagner; Manfred Kansy; Gabriele Cruciani
Journal:  Eur J Med Chem       Date:  2010-06-23       Impact factor: 6.514

6.  Structure of GES-1 at atomic resolution: insights into the evolution of carbapenamase activity in the class A extended-spectrum beta-lactamases.

Authors:  Clyde A Smith; Marisa Caccamo; Katherine A Kantardjieff; Sergei Vakulenko
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2007-08-17

7.  Molecular structure of the acyl-enzyme intermediate in beta-lactam hydrolysis at 1.7 A resolution.

Authors:  N C Strynadka; H Adachi; S E Jensen; K Johns; A Sielecki; C Betzel; K Sutoh; M N James
Journal:  Nature       Date:  1992-10-22       Impact factor: 49.962

8.  Structure-Based Virtual Screening for the Discovery of Novel Inhibitors of New Delhi Metallo-β-lactamase-1.

Authors:  Francesca Spyrakis; Giuseppe Celenza; Francesca Marcoccia; Matteo Santucci; Simon Cross; Pierangelo Bellio; Laura Cendron; Mariagrazia Perilli; Donatella Tondi
Journal:  ACS Med Chem Lett       Date:  2017-11-26       Impact factor: 4.345

9.  In silico identification and experimental validation of hits active against KPC-2 β-lactamase.

Authors:  Raphael Klein; Pasquale Linciano; Giuseppe Celenza; Pierangelo Bellio; Sofia Papaioannou; Jesus Blazquez; Laura Cendron; Ruth Brenk; Donatella Tondi
Journal:  PLoS One       Date:  2018-11-29       Impact factor: 3.240

10.  Kinetic and structural requirements for carbapenemase activity in GES-type β-lactamases.

Authors:  Nichole K Stewart; Clyde A Smith; Hilary Frase; D J Black; Sergei B Vakulenko
Journal:  Biochemistry       Date:  2014-12-22       Impact factor: 3.162

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  5 in total

1.  X-ray Crystallography Deciphers the Activity of Broad-Spectrum Boronic Acid β-Lactamase Inhibitors.

Authors:  Laura Cendron; Antonio Quotadamo; Lorenzo Maso; Pierangelo Bellio; Martina Montanari; Giuseppe Celenza; Alberto Venturelli; Maria Paola Costi; Donatella Tondi
Journal:  ACS Med Chem Lett       Date:  2019-03-27       Impact factor: 4.345

2.  Heteroaryl Phosphonates as Noncovalent Inhibitors of Both Serine- and Metallocarbapenemases.

Authors:  Orville A Pemberton; Priyadarshini Jaishankar; Afroza Akhtar; Jessie L Adams; Lindsey N Shaw; Adam R Renslo; Yu Chen
Journal:  J Med Chem       Date:  2019-09-13       Impact factor: 7.446

3.  Virtual screening identifies broad-spectrum β-lactamase inhibitors with activity on clinically relevant serine- and metallo-carbapenemases.

Authors:  Francesca Spyrakis; Matteo Santucci; Lorenzo Maso; Simon Cross; Eleonora Gianquinto; Filomena Sannio; Federica Verdirosa; Filomena De Luca; Jean-Denis Docquier; Laura Cendron; Donatella Tondi; Alberto Venturelli; Gabriele Cruciani; Maria Paola Costi
Journal:  Sci Rep       Date:  2020-07-29       Impact factor: 4.379

4.  Targeting the Class A Carbapenemase GES-5 via Virtual Screening.

Authors:  Raphael Klein; Laura Cendron; Martina Montanari; Pierangelo Bellio; Giuseppe Celenza; Lorenzo Maso; Donatella Tondi; Ruth Brenk
Journal:  Biomolecules       Date:  2020-02-14

5.  Phenylboronic Acids Probing Molecular Recognition against Class A and Class C β-lactamases.

Authors:  Pasquale Linciano; Mattia Vicario; Ivana Kekez; Pierangelo Bellio; Giuseppe Celenza; Isabel Martín-Blecua; Jesús Blázquez; Laura Cendron; Donatella Tondi
Journal:  Antibiotics (Basel)       Date:  2019-09-30
  5 in total

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